Synthesis and catalytic application of Pd complex catalysts: Atom‐efficient cross‐coupling of triarylbismuthines with haloarenes and acid chlorides under mild conditions

• Published in: Applied organometallic chemistry 2017-04, Vol.31 (4), p.np-n/a
• Main Authors: Jadhav, B.D., Pardeshi, S.K.
• Format: Article
• Language: English
• Subjects: Aromatic compounds; atom efficient; Bismuth; Catalysis; Catalysts; Chemical reactions; Chemical synthesis; Chemistry; Chlorides; Construction equipment; Coupling (molecular); Cross coupling; Economics; Halides; Infrared analysis; Infrared spectroscopy; Ligands; NMR; Nuclear magnetic resonance; organobismuth(III) compounds; Palladium; palladium complex catalysts; Spectroscopic analysis; Synthesis (chemistry); Transformations; transmetallation
• ISSN: 0268-2605; 1099-0739
• DOI: 10.1002/aoc.3591

Palladium‐catalysed cross‐coupling reactions are some of the most frequently used synthetic tools for the construction of new carbon–carbon bonds in organic synthesis. In the work presented, Pd(II) complex catalysts were synthesized from palladium chloride and nitrogen donor ligands as the precursors. Infrared and 1H NMR spectroscopic analyses showed that the palladium complexes were formed in the bidentate mode to the palladium centre. The resultant Pd(II) complexes were tested as catalysts for the coupling of organobismuth(III) compounds with aryl and acid halides leading to excellent yields with high turnover frequency values. The catalysts were stable under the reaction conditions and no degradation was noticed even at 150°C for one of the catalysts. The reaction proceeds via an aryl palladium complex formed by transmetallation reaction between catalyst and Ar3Bi. The whole synthetic transformation has high atom economy as all three aryl groups attached to bismuth are efficiently transferred to the electrophilic partner. Pd(II) complex catalysts were synthesized from palladium chloride and nitrogen donor ligands as precursors. The resultant Pd(II) complexes were tested as catalysts for the coupling of organobismuth(III) compounds with aryl and acid halides and led to excellent yield with high turnover frequency. The overall synthetic transformation has high atom economy as all three aryl groups attached to bismuth are efficiently transferred to the electrophilic partner.